Holiday rentals with a pool in Gillespie County

Upscale|Swimspa-pool|sauna|hot tub|2 blk to Main

Harmony is a gorgeous upscale home located two blocks from Main Street. The home has been custom designed to host families, couples, and friend getaways. Enjoy the open layout, spacious bedrooms and fantastic dining and kitchen areas this gorgeous has to offer. Step outside to your private backyard relaxation oasis featuring a swimspa pool, sauna, hot tub, spacious deck, sipping wine around the fire pit, or enjoying a hot cup of coffee on the front porch! Book your Hill Country getaway today!

Claret House, Hot tub, Fire pit, Cowboy Pool!

Claret House is a modern 1 bedroom home with an eclectic, artistic flair! This spacious yet cozy home has everything you need to relax and reconnect, even a small office if you need to do some work while you're away! Enjoy the hot tub or cowboy pool and soak any stress away! If you want to stay in and leave the hectic world behind, you can make a delicious meal in the fully equipped, large kitchen. And at the end of the day, rest well in the luxurious king-size bed! Managed by Heavenly Hosts

Tejas Hills Guest Haus #2 | Hill Country + Pool

POOL RETREAT | NEAR MAIN STREET | HILL COUNTRY ESCAPE Relax at Tejas Hills Guest Haus #2 — a charming 2BR/1BA Hill Country retreat in Fredericksburg, TX featuring a private pool and spacious backyard. Conveniently located just minutes from historic Main Street, local shops, and restaurants. Minutes from Wine Road 290 wineries, breweries, and Enchanted Rock. The perfect spot to unwind, sip local wine, and soak up the Hill Country sunshine with family, friends, or that special someone.

Airstream Glamping Near Town!

Are you looking for a fun, unique and instaworthy place to stay while in Fredericksburg? If so this is the place for you. Newley Renovated Vintage Airstream parked on our 7 acre compound just a quick 7 minuet drive to the Heart of Main Street. The interior has been completely redone with style and comfort. The perfect retreat for couples or friends who are looking for a non-traditional stay. Unwind after a long day of shopping and sight seeing in the cowboy pool while star gazing.

3Bed/2Bath Pool Hottub Right off Main Street

This exquisite townhouse is right off Main St, within WALKING distance to the heart of Fredericksburg including shops, restaurants and wineries! Enjoy your own PRIVATE courtyard with a PRIVATE splash pool, gas grill, outdoor TV, and hot tub!! Come relax in the luxurious interiors with a fireplace and stylish decor. We are pet friendly! A small pet fee of $50 per pet. This newly built Fredericksburg Farm Modern Sunday Haus has keyless entry for easy contactless check in.

Oak Casita in The Glades

Welcome to Oak Haus in The Glades on winery corridor. Take it easy at this unique and tranquil getaway. Enjoy wine at the fire pit or coffee on the porch, where deer might scamper by. Spend your time relaxing, playing games or swimming in the heated cowboy pool (which is a 10 foot stock tank) in the common leisure corral. Visit the 12 wineries, brewery or two distilleries that are within one and a half miles of Oak Haus. Fredericksburg is just a short drive away.

The Silo: Modern design, private, *heated pool*

Less than 3 miles from Main Street, The Silo rests on 40 acres in the wide open space of the Hill Country providing a unique get-away. Enjoy a breath-taking sunset as you stroll down the private granite road frequented by native wildlife and blackbucks, before heading to downtown Fredericskburg for fine dining, local wines, and one-of-a-kind shopping. We want your stay to be wonderful and are happy to share local recommendations for an authentic experience.

Luxury+Privacy+Pool+Near Town

Escape the hustle to this Guest House located on 15 private acres just a 5 minute drive to town in an exclusive gated subdivision. You'll love the tranquil setting and privacy all while being a short drive to Main Street. We hope this will be a restful and restorative place for couples to enjoy quality time together in a romantic setting or for someone to enjoy a quiet retreat alone in a peaceful setting. Follow us @revivalridge on IG ☀️

Pecan Treehouse @ A-Frame Ranch

Escape to a modern A-frame treehouse just outside Fredericksburg. Nestled on 17 acres, the Pecan Cabin offers Hill Country views, stargazing, and deer sightings, yet you’re minutes from Main St. Swim in the container pool, gather at the fire pit, or simply unwind on your private balcony. Inside, enjoy a king bed, dual rainfall shower, luxe linens, and modern amenities. The perfect blend of nature and comfort awaits.

3B/2B Pool & Hot Tub- 1 BLK to Main!

Cozy comfortable cottage one block from Main Street! Walking distance to popular restaurants, bars, shops and museums. Very convenient to wineries- perfect place for friend and family gatherings. Large backyard includes covered living space with fireplace and grill, private pool with hot tub, fire pit sitting area, and plenty of space for lawn games. You will feel right at home at the Henning Haus!

Chic Retreat, Pool, Hot Tub and Pet Friendly

Bachelorette Party? Wine Tasting? Family Vacation? Welcome to Acorn Haus, your stylish Fredericksburg retreat! Perfect for any occasion, this 3-bedroom gem is just minutes from historic Main Street and the heart of Texas wine country. With its unique modern farmhouse and boho-chic decor, every corner is designed for creating unforgettable moments. Dive into the heart of Fredericksburg with us! 💫

Private Home for 8 Stunning Pool

Welcome to Hendrix’s Hideout! This new build home offers a light and minimal design so that throughout your stay you can focus on taking in the beautiful Hill Country Views we are nestled in. Begin your day with a swim or end it by lounging pool side or maybe a round of corn hole. Either way we guarantee your favorite thing to do will be watching the sunset turn into a evening of star gazing.